[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid → HCID 57389905, compound
Reaction equation
CC([N:5]([C@H:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]([N:24]3[CH2:28][CH2:27][C@H:26]([NH:29]C(OC(C)(C)C)=O)[CH2:25]3)=[N:19][CH:20]=[C:21](Br)[CH:22]=2)(=[O:16])=[O:15])[CH2:10]1)C(=O)[O-])(C)C.[CH3:37][C:38]1([CH3:62])[CH2:47][CH2:46][C:45]2[N:44]=[CH:43][N:42]=[C:41]([N:48]3[CH2:54][C:53]4[CH:55]=[C:56](B(O)O)[CH:57]=[CH:58][C:52]=4[O:51][CH2:50][CH2:49]3)[C:40]=2[CH2:39]1>>[NH2:29][C@H:26]1[CH2:27][CH2:28][N:24]([C:18]2[C:17]([S:14]([N:11]3[CH2:12][CH2:13][C@H:9]([NH2:5])[CH2:10]3)(=[O:16])=[O:15])=[CH:22][C:21]([C:56]3[CH:57]=[CH:58][C:52]4[O:51][CH2:50][CH2:49][N:48]([C:41]5[C:40]6[CH2:39][C:38]([CH3:37])([CH3:62])[CH2:47][CH2:46][C:45]=6[N:44]=[CH:43][N:42]=5)[CH2:54][C:53]=4[CH:55]=3)=[CH:20][N:19]=2)[CH2:25]1Participants
3
Procedure
Prepared according to the method of example 5 by using 1,1-dimethylethyl[(3S)-1-({5-bromo-2-[(3S)-3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)pyrrolidin-1-yl]pyridin-3-yl}sulfonyl)pyrrolidin-3-yl]carbamate (reagent preparation 40) and [4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid (reagent preparation 23) in step 1. 1H NMR (400 MHz, Methanol-d4): 8.56 (s, 1H), 8.55 (s, 1H), 8.53 (s, 1H), 7.74 (s, 1H), 7.52 (d, 1H), 7.01 (d, 1H), 5.12 (s, 2H), 4.47 (m, 2H), 4.32 (m, 3H), 4.22 (m, 1H), 4.05 (m, 2H), 3.85 (m, 1H), 3.74 to 3.56 (m, 5H), 2.85 (t, 2H), 2.59 (s, 2H), 2.35 (m, 2H), 2.22 (m, 2H), 1.70 (t, 2H), 0.93 (s, 6H); MS (EI) for C32H42N8O3S: 619 (MH+).
Workup
- customPrepared
Sources & evidence
- ORD record
- ord-96fde441c91d44388f8cc1fa5fff336a
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08648066B2
Reaction notes
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